'Confessions of a Dangerous Mind' | 2002

In his directorial debut, Clooney took the helm of the comedy biopic "Confessions of a Dangerous Mind." Actor Sam Rockwell, pictured, portrays legendary game show host Chuck Barris and his secret life as a CIA assassin. Drew Barrymore, pictured, and Julia Roberts also star. The film earned the respect of critics but did terribly at the box office. Clooney met soap opera actress Krista Allen on set and the pair dated for two years.

In his directorial debut, Clooney took the helm of the comedy biopic "Confessions of a Dangerous Mind." Actor Sam Rockwell, pictured, portrays legendary game show host Chuck Barris and his secret life as a CIA assassin. Drew Barrymore, pictured, and Julia Roberts also star. The film earned the respect of critics but did terribly at the box office. Clooney met soap opera actress Krista Allen on set and the pair dated for two years. (Takashi Seida / Miramax)

In his directorial debut, Clooney took the helm of the comedy biopic "Confessions of a Dangerous Mind." Actor Sam Rockwell, pictured, portrays legendary game show host Chuck Barris and his secret life as a CIA assassin. Drew Barrymore, pictured, and Julia Roberts also star. The film earned the respect of critics but did terribly at the box office. Clooney met soap opera actress Krista Allen on set and the pair dated for two years.Takashi Seida / Miramax